JP7115611B2 - Composition - Google Patents

Description

The present invention relates to compositions.

Hydrochlorofluorocarbons (HCFCs) are expected to be regulated due to their detrimental effect on the ozone layer. HCFCs include 3,3-dichloro-1,1,1,2,2-pentafluoropropane (HCFC-225ca), 1,3-dichloro-1,1,2,2,3-pentafluoropropane (HCFC- 225cb) and the like. With the regulation of HCFCs, development of alternative compounds is desired.

Compounds that can replace HCFCs include, for example, 1-chloro-2,3,3-trifluoropropene (HCFO-1233yd). HCFO-1233yd has a low global warming potential (GWP) and can be suitably used for applications such as cleaning agents, solvents, refrigerants, foaming agents and aerosols.

HCFO-1233yd has structural isomers, Z-isomer of HCFO-1233yd (HCFO-1233yd(Z)) and E-isomer of HCFO-1233yd (HCFO-1233yd(E)). Of these, HCFO-1233yd(Z) is primarily used in detergent, solvent, refrigerant, blowing agent and aerosol applications.

Patent Document 1 discloses 1,1,2,2,3-pentafluoropropane (HCFC-245ca) from 1-chloro-2,2,3,3-tetrafluoropropane (HCFC-244ca) and hydrogen fluoride. is disclosed. Since HCFO-1233yd is produced as a by-product in this method, a composition containing HCFO-1233yd can be obtained by separating HCFO-1233yd from the composition obtained by the above method.

HCFO-1233yd produced by the above method is a mixture of HCFO-1233yd (E) and HCFO-1233yd (Z). It is preferable to be able to adjust the composition of the mixture. However, Patent Document 1 does not describe separation of HCFO-1233yd(E) and HCFO-1233yd(Z) or adjustment of the composition.

In addition, water may be mixed in the manufacturing process of HCFO-1233yd. Water (moisture) in compositions containing HCFO-1233yd(Z) leads to reduced reliability and performance and various problems when used as cleaning agents, solvents, refrigerants, blowing agents or aerosols. can cause It is preferred to keep the water content as low as possible so as not to cause such undesirable effects.

Distillation is usually used to remove by-products from the reaction product by utilizing the difference in boiling points. It is about 48°C and the boiling point is close. Therefore, it is difficult to separate HCFO-1233yd(E) using a conventional distillation column, and a method for removing HCFO-1233yd(E) more efficiently has been desired.

In addition, since a mixture of HCFO-1233yd(Z) and water forms an azeotrope-like composition, separation by distillation is difficult, and a method for efficiently removing water has been sought.

WO 1994/14737

The present invention has been made to solve the above problems, and a composition containing HCFO-1233yd(Z), HCFO-1233yd(E) and water is prepared by removing HCFO-1233yd(E) and water. An object of the present invention is to provide a method for producing HCFO-1233yd(Z) which can be removed efficiently, has a high recovery rate of HCFO-1233yd(Z), and increases the purity of HCFO-1233yd(Z).

The present invention provides a method for producing HCFO-1233yd(Z) having the following structure.
[1] Distilling a distillation composition containing HCFO-1233yd (Z), HCFO-1233yd (E), and water to convert the HCFO-1233yd (E) and the water into an azeotropic composition or an azeotropic composition A method for producing HCFO-1233yd(Z), characterized in that it is removed as a boiling-like composition.
[2] According to [1], in the composition for distillation, the ratio of the water content to the sum of the HCFO-1233yd (E) content and the water content is 0.001 to 5% by mass. Method for producing HCFO-1233yd(Z).
[3] The HCFO- of [1] or [2], wherein the distillation composition is prepared by adding HCFO-1233yd (E) to a composition containing HCFO-1233yd (Z) and water. A method for producing 1233yd(Z).
[4] The distillation according to [1] or [2], wherein the distillation composition is prepared by adding water to a composition containing HCFO-1233yd(Z) and HCFO-1233yd(E). 1233yd(Z) composition for manufacturing.
[5] The composition according to any one of [1] to [4], wherein the distillation composition is prepared using a reaction composition containing 1233yd(Z) obtained by dehydrofluorination of HCFC-244ca. Method for producing HCFO-1233yd(Z).
[6] The method for producing HCFO-1233yd(Z) according to any one of [1] to [5], wherein the distillation is performed in a distillation column with a top temperature of 40 to 55°C.

According to the method for producing HCFO-1233yd(Z) of the present invention, HCFO-1233yd(E) and water are efficiently produced from a composition containing HCFO-1233yd(Z), HCFO-1233yd(E), and water. It can be removed well, the recovery of HCFO-1233yd(Z) can be increased, and the purity of HCFO-1233yd(Z) can be increased.

It is a figure which shows an example of the distillation apparatus used for the manufacturing method of embodiment.

In this specification, 1-chloro-2,3,3-trifluoropropene (HCFO-1233yd) is also simply referred to as "1233yd". Further, the Z-isomer of HCFO-1233yd, which is a structural isomer of HCFO-1233yd, is also simply referred to as "1233yd(Z)", and the E-isomer of HCFO-1233yd is simply referred to as "1233yd(E)".
In the present specification, with respect to halogenated hydrocarbons, when an abbreviation of the compound is written in parentheses following the name of the compound, the abbreviation is used in place of the name of the compound as necessary. In addition, compounds having double bonds in the molecule and having E- and Z-isomers are represented by (E) and (Z) at the end of the compound abbreviations, respectively. If there is no (E) or (Z) notation at the end of the abbreviation of the compound name, it is either the (E) isomer, the (Z) isomer, or a mixture of the (E) isomer and the (Z) isomer. indicates

BEST MODE FOR CARRYING OUT THE INVENTION Embodiments of the present invention will be described below.
In the method for producing 1233yd(Z) of the present embodiment, a composition for distillation containing 1233yd(Z), 1233yd(E), and water is distilled, and 1233yd(E) and water are produced from the composition for distillation. is removed as an azeotropic or azeotrope-like composition. Here, the azeotropic or azeotrope-like composition of 1233yd(E) and water may be partially removed or entirely removed.

First, an azeotropic composition and an azeotrope-like composition will be described.

In general, an azeotropic composition is a mixture in which the composition of the gas phase generated by vaporizing the liquid phase is the same as the composition of the liquid phase, or the composition of the liquid phase generated by liquefying the gas phase is the same as the composition of the gas. It is defined as being identical to the phase composition. Azeotropic compositions are suitable for distillation and reflux because the composition does not change due to evaporation or condensation. In addition, the composition of the azeotropic composition changes depending on the pressure conditions.

On the other hand, azeotrope-like compositions exhibit behavior similar to azeotrope compositions. That is, the azeotrope-like composition is such that the composition of the gas phase generated by vaporization of the liquid phase is substantially the same as the composition of the liquid phase, or the composition of the liquid phase generated by liquefying the gas phase is the same as the composition of the gas phase. is almost the same as the composition of An azeotrope-like composition can be suitably used for distillation and reflux, like the azeotrope composition, because the composition hardly changes due to evaporation or condensation.

The inventors have found that 1233yd(E) and water form an azeotropic or azeotrope-like composition. Furthermore, the azeotropic or azeotrope-like composition of 1233yd(E) and water is preferentially formed over the azeotrope or azeotrope-like composition of 1233yd(Z) and water. Found it.

An azeotropic or azeotrope-like composition of 1233yd(E) and water has a lower boiling point than 1233yd(Z). That is, while the boiling point of 1233yd(Z) is about 54°C, the boiling point of an azeotropic or azeotrope-like composition of 1233yd(E) and water is about 40 to 48°C. In addition, a boiling point is a boiling point under atmospheric pressure. Atmospheric pressure is 101.325 kPa.

Therefore, by utilizing an azeotropic or azeotrope-like composition of 1233yd(E) and water, 1233yd(Z) can be separated from 1233yd(E) and water. Thereby, 1233yd(E) and water can be efficiently removed from the distillation composition, the recovery rate of 1233yd(Z) can be increased, and the purity of 1233yd(Z) can be increased.

The azeotropic composition of 1233yd(E) and water has a relative volatility of 1.00 represented by the following formula (1) under atmospheric pressure. The similar composition has a relative volatility represented by the following formula (1) within the range of 1.00±0.20. The azeotrope-like composition can obtain substantially the same effects as the azeotrope composition, provided that the relative volatility is within the above range.

Relative volatility = (mol% of water in gas phase/mol% of 1233yd(E) in gas phase)/(mol% of water in liquid phase/mol% of 1233yd(E) in liquid phase) (1)

The composition range that allows obtaining the desired relative volatility can be determined as follows. First, the composition of the mixture of 1233yd(E) and water is gradually changed, and the compositions of the liquid phase and the gas phase are measured with a Karl Fischer moisture meter or gas chromatograph. Using the liquid phase and gas phase compositions, the relative volatility is obtained from the above formula (1). This provides a correlation between composition and relative volatility. From this correlation, the composition for the desired relative volatility can be determined.

The azeotropic composition and azeotrope-like composition of 1233yd(E) and water have a water content ratio of 0.001 to 5% by mass with respect to the total content of 1233yd(E) and water. Preferably. When the ratio is within the above range, the relative volatility tends to be within the range of 1.00±0.20, and the boiling point tends to be about 40 to 48°C. From the viewpoint of lowering the boiling point by bringing the relative volatility closer to 1.00, the above ratio is more preferably 0.01 to 2.5% by mass, more preferably 0.05 to 2% by mass, 0.1 to 2% by mass is particularly preferred.

Next, the composition for distillation will be explained.

The distillation composition contains 1233yd(Z), 1233yd(E), and water. The composition for distillation is a composition containing at least one selected from 1233yd (E) and water and 1233yd (Z), and optionally at least one selected from 1233yd (E) and water. may be prepared by

1233yd can be obtained, for example, by the method disclosed in WO 1994/14737. That is, 1-chloro-2,2,3,3-tetrafluoropropane (HCFC-244ca) and hydrogen fluoride are supplied in the presence of a chromium hydroxide catalyst to obtain 1,1,2,2,3-penta It can be obtained as a by-product in the production of fluoropropane (HCFC-245ca).

Further, 1233yd can be obtained, for example, by dehydrofluorination reaction of HCFC-244ca. The above reaction can be carried out at a temperature of 40 to 80° C. using, for example, potassium hydroxide, sodium hydroxide, etc. as a reactant.

1233yd obtained by these production methods is usually a mixture of 1233yd(Z) and 1233yd(E), and may be contaminated with water during the production process. That is, a reaction composition containing 1233yd(Z) and at least one selected from 1233yd(E) and water is obtained by the above production method. The reaction composition obtained by the above method may be used as it is as a composition for distillation, or depending on the content of water and 1233yd (E) contained in the reaction composition, You may use what was prepared by adding at least 1 type selected as a composition for distillation.

Reactive compositions can be classified as follows. That is, a reaction composition (first reaction composition) containing 1233yd(Z) and water but no 1233yd(E), a reaction composition containing 1233yd(Z) and 1233yd(E) and no water It can be divided into reaction compositions (second reaction compositions), 1233yd(Z), 1233yd(E), and reaction compositions containing water (third reaction compositions).

If the first reaction composition, ie, contains 1233yd(Z) and water and no 1233yd(E), the distillable composition can be obtained by adding 1233yd(E). By adding 1233yd(E), an azeotropic or azeotrope-like composition of 1233yd(E) and water can be formed.

If the second reaction composition, ie, contains 1233yd(Z) and 1233yd(E) and no water, the distillable composition can be obtained by adding water. Addition of water can form an azeotropic or azeotrope-like composition of 1233yd(E) and water.

If it contains a third reaction composition, namely 1233yd(Z), water, and 1233yd(E), it can be made into a composition for distillation as is. In addition, at least one selected from 1233yd(E) and water can be added to the third reaction composition according to the contents of water and 1233yd(E).

The content of 1233yd (Z) in the distillation composition used in the present embodiment is preferably 50% by mass or more, more preferably 80% by mass or more, relative to the total amount of the distillation composition. 90% by mass or more is more preferable. If the content of 1233yd(Z) is at least the above lower limit, 1233yd(E) and water can be removed efficiently.
The respective contents of water and 1233 yd (E) in the composition for distillation are not necessarily limited. By including water and 1233yd(E) in the distillation composition, an azeotropic or azeotrope-like composition can be formed from water and 1233yd(E).

It is preferable that all of the 1233yd(E) and water contained in the distillation composition form an azeotropic composition or an azeotrope-like composition and be efficiently removed from the distillation composition. From this point of view, in the distillation composition, the ratio of the water content to the total of the 1233yd (E) content and the water content is preferably 0.001 to 5% by mass. 0.01 to 2.5% by mass, more preferably 0.05 to 2% by mass, and particularly preferably 0.1 to 2% by mass.

The proportion of water can be adjusted by adding 1233yd(E) or water. For example, if the proportion of water is low, the proportion of water can be increased by adding water. Moreover, when the proportion of water is high, the proportion of water can be reduced by adding 1233yd(E).

The distillation composition may contain components other than 1233yd(Z), 1233yd(E) and water. Examples of components other than 1233yd(Z), 1233yd(E) and water include raw materials for producing 1233yd(Z), by-products produced other than 1233yd(Z) and 1233yd(E), and the like. Components other than 1233yd (Z), 1233yd (E) and water specifically include HCFC-244ca, 1-chloro-3,3-difluoro-1-propyne, 1,1,2,2,3- Alcohols such as pentafluoropropane, 2,3,3-trifluoro-1-propene, 1,2,3,3-tetrafluoro-1-propene, tetrafluoropropanol, and methanol are included. Components other than 1233yd (Z), 1233yd (E), and water are preferably 30% by mass or less with respect to the total amount of the distillation composition from the viewpoint of increasing the recovery rate of 1233yd (Z), and 10 mass % or less. In particular, alcohols such as tetrafluoropropanol and methanol may inhibit the formation of an azeotropic composition of 1233yd (E) and water. On the other hand, it is preferably 5% by mass or less, more preferably 1% by mass or less.

Next, distillation will be explained.

In the method for producing 1233yd(Z) of the present embodiment, distillation is performed using a distillation composition containing 1233yd(Z), 1233yd(E), and water. By allowing 1233yd(E) and water to coexist in the distillation composition, an azeotropic or azeotrope-like composition of 1233yd(E) and water can be formed.

While the boiling point of 1233yd (Z) is about 54 ° C., the boiling point of the azeotropic composition or azeotrope-like composition of 1233yd (E) and water is about 40 to 48 ° C. Distilling the composition can remove at least a portion of the azeotropic or azeotrope-like composition of 1233yd(E) and water from the composition for distillation. The result is a composition with reduced 1233yd(E) and water content, ie, pure 1233yd(Z).

Any known distillation apparatus may be used as long as it can remove at least part of the azeotropic composition or azeotrope-like composition of 1233yd(E) and water from the composition for distillation.

FIG. 1 shows an example of a distillation apparatus.
The distillation apparatus 10 has, for example, a distillation column 11. The distillation column 11 includes a pipe 12 for supplying a composition for distillation, a pipe 13 for taking out a distillate from the top of the distillation column 11, and a distillation column. A pipe 14 for taking out the bottom product from the bottom of the column 11 is connected. The distillation apparatus 10 may be either batch type or continuous type. Further, the distillation column 11 may be either hollow type or multi-stage type.

In such a distillation apparatus 10, for example, a distillate containing an azeotropic composition or an azeotrope-like composition of 1233 yd (E) and water can be obtained from the top, and 1233 yd A can product containing (Z) can be obtained.

In addition, when the composition for distillation contains excess 1233yd (E) or water exceeding the composition range of the azeotropic composition or azeotrope-like composition of 1233yd (E) and water, these Excess 1233yd(E) or water may be contained, for example, in the bottoms bottoms.

In the case of the multi-stage distillation column 10, the composition for distillation is usually supplied to the middle stage of the multi-stage distillation column 10. In this case, a distillate containing an azeotropic or azeotrope-like composition of 1233yd(E) and water can be obtained from a stage above the stage to which the distilling composition is fed. The bottoms containing 1233yd(Z) can also be obtained from a stage below the stage to which the distillation composition is fed.

The pressure during distillation is preferably 0.1 to 1.0 MPa in terms of absolute pressure. At such a pressure, the top temperature of the distillation column is preferably 40-80°C. By setting the pressure during distillation and the top temperature of the distillation column within the above ranges, at least part of the azeotropic composition or azeotrope-like composition of 1233yd (E) and water is efficiently removed from the distillation composition. can be removed well.

For example, when the pressure during distillation is 0.1 MPa in absolute pressure, the top temperature of the distillation column is 1233 yd (E) and water recovery of distillate containing an azeotropic composition or azeotrope-like composition From the viewpoint of increasing the amount, the temperature is preferably 40°C or higher, more preferably 43°C or higher, and even more preferably 45°C or higher. From the viewpoint of reducing the ratio of 1233yd(Z) contained in the distillate, the temperature is preferably 55°C or lower, more preferably 52°C or lower, even more preferably 50°C or lower, and most preferably 48°C or lower.

Distillation can be carried out again using the bottoms containing 1233yd(Z) as the distillation composition. When the bottom product contains 1233yd (E) and water, distillation can be performed to separate the 1233yd (E) and water, and the bottom product with an increased purity of 1233yd (Z) is obtained. Obtainable.

Further, by using the distillate containing 1233yd(E) as a distillation composition and distilling again, a distillate with an increased ratio of 1233yd(E) and water can be obtained. Further, by dehydrating the obtained distillate by the method described later or the like, 1233yd(E) with high purity can be obtained.

In the method for producing 1233yd(Z) according to the present embodiment, the recovery rate of bottoms can be increased to 83% or more by distillation. The recovery rate of bottoms is preferably 84% or more, more preferably 85% or more. Here, the recovery rate [%] of the bottoms is determined by the following formula from the amount of the distillation composition supplied and the amount of the bottoms recovered.
Recovery rate of bottoms [%] = (amount of bottoms recovered) / (amount of distillation composition supplied) x 100

In addition, in the method for producing 1233yd(Z) of the present embodiment, distillation can increase the recovery rate of 1233yd(Z) in the bottom product to 85% or more, for example. The recovery rate of 1233yd(Z) in the bottom product is preferably 90% or more, more preferably 95% or more. Here, the recovery rate [%] of 1233yd (Z) in the bottoms is obtained by the following formula from the supply amount of 1233yd (Z) in the distillation composition and the recovery amount of 1233yd (Z) in the bottoms: required by
Recovery rate [%] of 1233 yd (Z) in bottoms = (amount of 1233 yd (Z) recovered in bottoms)/(supply amount of 1233 yd (Z) in distillation composition) x 100

Furthermore, according to such distillation, for example, the ratio of the content of 1233yd (Z) to the total content of 1233yd (Z), 1233yd (E) and water in the bottom product (purity of 1233yd (Z)) can be 80% by mass or more. The ratio is preferably 90% by mass or more, more preferably 93% by mass or more, still more preferably 95% by mass or more, and most preferably 98% by mass.

By contacting the bottoms obtained by distillation with a solid adsorbent, the water content in the bottoms can be reduced. Examples of solid adsorbents include silica. Silica is a substance with a chemical composition predominantly of _SiO2 . Examples of silica include porous synthetic silica gel, mesoporous silica, silica alumina, and the like. One type of silica may be used alone, or two or more types may be used in combination. The shape of silica is not particularly limited, and examples thereof include powder, fine particles, granules, thin films, and the like.

The present invention will be described in detail below with reference to examples. However, the present invention is not limited by these examples.

(Example 1)
As a distillation column, a multi-stage distillation column having 50 theoretical plates was prepared. A composition for distillation was supplied at a rate of 1.0 kg/h from the 40th stage from the top of the distillation column. As a composition for distillation, as shown in Table 1, 0.8800 kg/h of 1233 yd(Z), 0.0050 kg/h of water, and 0.1150 kg/h of 1233 yd(E) were supplied. Thereafter, continuous distillation was performed with the operating pressure set to atmospheric pressure and the column top temperature set to 45.5°C.

During the distillation, a distillate was withdrawn from the top of the tower and a bottom product was withdrawn from the bottom of the tower. Then, with respect to the distillate and the bottom product, a Karl Fischer moisture meter was used to determine the amount of water recovered, and gas chromatography was used to determine the amount of 1233 yd (Z) and 1233 yd (E) recovered. Also, the recovery rate (collected amount/supplied amount) was obtained from the supplied amount and the collected amount.

Table 1 shows the amount of the distillation composition supplied and the amount and rate of recovery of the distillate and the bottom product, respectively. In addition, Table 2 shows the composition for distillation, the composition of the distillate and the bottom product, and the proportion of water in 1233 yd (E) and water.

In addition, the composition of the composition for distillation is obtained from the supply amount of each component. The composition of the distillate and the bottom product is obtained from the recovered amount of each component. The proportion of water in 1233yd(E) and water is obtained from the amount of supply or recovery of 1233yd(E) and water.

As is clear from Tables 1 and 2, by using a distillation composition containing 1233yd (Z), 1233yd (E), and water, it is possible to increase the recovery rate of the bottoms to 83% by mass or more. In addition, the content of 1233yd(Z) in the bottom product can be made 85% by mass or more.

(Example 2)
As shown in Table 3, distillation and measurement were performed in the same manner as in Example 1, except that the amount of each component supplied in the distillation composition was changed and the top temperature was set to 47.5 ° C. . Table 3 shows the recovery amount and recovery rate of distillate and bottom product, respectively. In addition, Table 4 shows the composition for distillation, the composition of the distillate and the bottom product, and the ratio of water in 1233 yd (E) and water, respectively.

As is clear from Tables 3 and 4, by using a distillation composition containing 1233yd (Z), 1233yd (E), and water, it is possible to increase the recovery rate of the bottoms to 83% by mass or more. In addition, the content of 1233yd(Z) in the bottom product can be made 85% by mass or more.

(Example 3)
As shown in Table 5, distillation and measurement were performed in the same manner as in Example 1, except that the amount of each component supplied in the distillation composition was changed and the top temperature was set to 51.5 ° C. . Table 5 shows the recovery amount and recovery rate of the distillate and the bottom product, respectively. In addition, Table 6 shows the composition for distillation, the composition of the distillate and the bottom product, and the proportion of water in 1233 yd (E) and water, respectively.

As is clear from Tables 5 and 6, by using a distillation composition containing 1233yd (Z), 1233yd (E), and water, the bottom product recovery rate can be made 83% by mass or more. In addition, the content of 1233yd(Z) in the bottom product can be made 85% by mass or more.

(Example 4)
As shown in Table 7, distillation and measurement were performed in the same manner as in Example 1, except that the amount of each component supplied in the distillation composition was changed. The distillation composition used in Example 4 was obtained by contacting 1-chloro-2,2,3,3-tetrafluoropropane with an aqueous potassium hydroxide solution at 50° C. to cause a dehydrofluorination reaction. rice field. When the crude liquid after the dehydrofluorination reaction was analyzed, in addition to 1233yd(Z) and 1233yd(E), unreacted HCFC-244ca and 1233yd as a by-product were further dehydrofluorinated 1-chloro -3,3-difluoropropyne, 1233yd to which tetrafluoropropanol (TFPO) was added, followed by dehydrofluorination, or 1-chloro-3,3-difluoropropyne to which TFPO was added, the molecular formula CHCl=C A compound represented by (CHF ₂ )OCH ₂ CF ₂ CHF ₂ (hereinafter referred to as 1233yd-TFPO adduct) was included.
Table 7 shows the recovery amount and recovery rate of the distillate and the bottom product, respectively. In addition, Table 8 shows the composition for distillation, the composition of the distillate and the bottom product, and the proportion of water in 1233 yd (E) and water, respectively.

As is clear from Tables 7 and 8, even if the reaction composition obtained by dehydrofluorinating 1-chloro-2,2,3,3-tetrafluoropropane is used as a distillation composition, It was found that the product recovery rate can be made 83% by mass or more, and the content ratio of 1233yd(Z) in the bottom product can be made 85% by mass or more.

(Comparative example 1)
As shown in Table 9, distillation and measurement were performed in the same manner as in Example 1, except that the amount of each component supplied in the distillation composition was changed and the top temperature was set to 53.0 ° C. . Table 9 shows the recovery amounts and recovery rates of distillates and bottoms. In addition, Table 10 shows the composition for distillation, the distillate, the composition of the bottom product, and the proportion of water in 1233 yd (E) and water.

As is clear from Tables 9 and 10, the distillation composition of Comparative Example 1 contains 1233yd (Z) and water, but does not contain 1233yd (E). When 1233yd(E) is not contained in this manner, the recovery rate of the bottoms is lower than when 1233yd(E) is contained. Moreover, it turns out that 1233yd(Z) and water are not fully separated.

According to the present invention, 1233yd(E) and water can be efficiently removed, the recovery rate of 1233yd(Z) can be increased, and the purity of 1233yd(Z) can be increased. Therefore, 1233yd(Z) can be effectively used in a wide range of fields such as detergents, solvents, and refrigerants.

10... Distillation apparatus, 11... Distillation column, 12, 13, 14... Piping.

Claims (5)

A composition comprising (Z)-1-chloro-2,3,3-trifluoro-1-propene, (E)-1-chloro-2,3,3-trifluoro-1-propene and water ,
The content of the (Z)-1-chloro-2,3,3-trifluoro-1-propene is the same as the (Z)-1-chloro-2,3,3-trifluoro-1-propene and the ( E) A composition characterized by containing 90% by mass or more of the total content of -1-chloro-2,3,3-trifluoro-1-propene and water. 2. The composition according to claim 1, wherein the water content is 0.01% by mass or less relative to the total amount of the composition. The content of the (Z)-1-chloro-2,3,3-trifluoro-1-propene is the same as the (Z)-1-chloro-2,3,3-trifluoro-1-propene and the ( E) The composition according to claim 1 or 2, which is 93% by mass or more based on the total content of -1-chloro-2,3,3-trifluoro-1-propene and water. The content of the (Z)-1-chloro-2,3,3-trifluoro-1-propene is the same as the (Z)-1-chloro-2,3,3-trifluoro-1-propene and the ( E) 95% by mass or more of the total content of -1-chloro-2,3,3-trifluoro-1-propene and water, according to any one of claims 1 to 3 composition. The content of the (Z)-1-chloro-2,3,3-trifluoro-1-propene is the same as the (Z)-1-chloro-2,3,3-trifluoro-1-propene and the ( E) 98% by mass or more of the total content of -1-chloro-2,3,3-trifluoro-1-propene and water, according to any one of claims 1 to 4 composition.

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